Some time ago, I had a '50s 7 1/2 that was hard (stiff) to pull over, but ran very well once started. It felt very stiff -- smooth but stiff -- until there was some fuel flowing into the cylinders with repeated cranking (at least that was my sense). I don't know whether it was an issue with rings, or an internal problem -- didn't seem to have any running issues at all once fired up, so didn't check any further. Once started, is yours running well?
You could have a restriction under the flywheel -- driver coil could be binding against the flywheel, for example. If there is a restriction like that, you should be able to feel it by slowly turning the flywheel clockwise by hand. Good to do that while the plugs are still out -- and a good time to check compression too.
I take it, yours is a manual start only. (If you are talking about an electric start motor, maybe the issue is the starting circuit (low battery, poor connection, starter windings). If it spins easily with the plugs out, it's likely the starting system.)